[(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 1054653-06-3
• Molecular Formula: C₂₄H₃₀N₂O₆
• Molecular Weight: 442.512

Synonyms:[(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester

There total 10 articles about [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

{(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-2-thioxo-[1,3]dioxolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester (211994-14-8) → [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester (1054653-06-3) + {(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-[1,3]dioxolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester + {(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-2-oxo-[1,3]oxathiolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester + ((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester (211994-16-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1.16667h; Heating;

DOI:10.1021/jo971562c

Reference yield:

2,5-diazido-2,5-dideoxy-1,6-di-O-phenyl-L-iditol (211993-84-9) → [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester (1054653-06-3)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / ethyl acetate / 16 h

2: 28 percent / Et₃N / CH₂Cl₂ / Ambient temperature

3: 0.050 g / CrO₃, Ac₂O, pyridine / CH₂Cl₂ / 3 h

4: 1.) NaBH₄, 2.) Ba(OH)2*8H₂O / 1.) MeOH, 1 h, 2.) H₂O, 80 deg C, 24 h

5: ethyl acetate / 4 h

6: 70 percent / tetrahydrofuran / 22 h / 55 °C

7: Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 0.83 h / Heating

With pyridine; chromium(VI) oxide; barium dihydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic anhydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo971562c

Reference yield:

2,5-diazido-2,5-dideoxy-3,4-O-isopropylidene-1,6-di-O-phenyl-L-iditol (211993-82-7) → [(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester (1054653-06-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / acetyl chloride / methanol / 24 h / Ambient temperature

2: H₂ / Pd/C / ethyl acetate / 16 h

3: 28 percent / Et₃N / CH₂Cl₂ / Ambient temperature

4: 0.050 g / CrO₃, Ac₂O, pyridine / CH₂Cl₂ / 3 h

5: 1.) NaBH₄, 2.) Ba(OH)2*8H₂O / 1.) MeOH, 1 h, 2.) H₂O, 80 deg C, 24 h

6: ethyl acetate / 4 h

7: 70 percent / tetrahydrofuran / 22 h / 55 °C

8: Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 0.83 h / Heating

With pyridine; chromium(VI) oxide; barium dihydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic anhydride; triethylamine; acetyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo971562c

upstream raw materials:

{(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-2-thioxo-[1,3]dioxolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester

2,5-diazido-2,5-dideoxy-1,6-di-O-phenyl-L-iditol

2,5-diazido-2,5-dideoxy-3,4-O-isopropylidene-1,6-di-O-phenyl-L-iditol

(2S,3R,4R,5S)-2,5-Diazido-1,6-bis-(4-nitro-phenoxy)-hexane-3,4-diol

Downstream raw materials:

((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

4-Nitro-benzoic acid (1R,3R)-3-tert-butoxycarbonylamino-1-((S)-1-tert-butoxycarbonylamino-2-phenoxy-ethyl)-4-phenoxy-butyl ester

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